Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCOCOCCOc1ccc(Nc2ncc(F)c(Nc3cccc(N(C)C(=O)OC(C)(C)C)c3)n2)cc1
InChiKey
QXPMIBJMJGRBJM-UHFFFAOYSA-N
Route Signature
006356452906fe173f51349387315012e5e672285840eec279fee81f55f0ddb1
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_58235ab7dcf90f2aaf4aed0f",
"signature": "006356452906fe173f51349387315012e5e672285840eec279fee81f55f0ddb1",
"contentHash": "257a5fd301b48b0f6cabb86639a076a40acdb22193203964218789bea1275bdc",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_1b5957800a9a5472221d60b0",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00388",
"moleculeId": "sa_0c77282be5c491fa94c515d1",
"smiles": "COCCOCOCCOc1ccc(Nc2ncc(F)c(Nc3cccc(N(C)C(=O)OC(C)(C)C)c3)n2)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_0c77282be5c491fa94c515d1",
"inchikey": "QXPMIBJMJGRBJM-UHFFFAOYSA-N",
"smiles": "COCCOCOCCOc1ccc(Nc2ncc(F)c(Nc3cccc(N(C)C(=O)OC(C)(C)C)c3)n2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "739",
"routeId": "sa_58235ab7dcf90f2aaf4aed0f",
"moleculeId": "sa_0c77282be5c491fa94c515d1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0c77282be5c491fa94c515d1",
"inchikey": "QXPMIBJMJGRBJM-UHFFFAOYSA-N",
"smiles": "COCCOCOCCOc1ccc(Nc2ncc(F)c(Nc3cccc(N(C)C(=O)OC(C)(C)C)c3)n2)cc1"
},
"smiles": "COCCOCOCCOc1ccc(Nc2ncc(F)c(Nc3cccc(N(C)C(=O)OC(C)(C)C)c3)n2)cc1",
"reactionStepId": "sa_0a13298e536de266cceb1ad0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150374690A1;0447;1807083\",\"rsmi\":\"Cl[c:16]1[n:17][cH:18][c:19]([F:20])[c:21]([NH:22][c:23]2[cH:24][cH:25][cH:26][c:27]([N:28]([CH3:29])[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37]2)[n:38]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH2:15])[cH:39][cH:40]1>C1COCCO1.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([F:20])[c:21]([NH:22][c:23]3[cH:24][cH:25][cH:26][c:27]([N:28]([CH3:29])[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37]3)[n:38]2)[cH:39][cH:40]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[n:17][cH:18][c:19]([F:20])[c:21]([NH:22][c:23]2[cH:24][cH:25][cH:26][c:27]([N:28]([CH3:29])[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37]2)[n:38]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH2:15])[cH:39][cH:40]1>C1COCCO1.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([F:20])[c:21]([NH:22][c:23]3[cH:24][cH:25][cH:26][c:27]([N:28]([CH3:29])[C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[cH:37]3)[n:38]2)[cH:39][cH:40]1\"}",
"reactionStep": {
"id": "sa_0a13298e536de266cceb1ad0",
"reactionHash": "35b02de83596bf791ad5cf694837ae43a3883c66608cdf55b89b0729deb4e122"
},
"children": [
{
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"routeId": "sa_58235ab7dcf90f2aaf4aed0f",
"moleculeId": "sa_9ae70c5f8c8f02f7fc61047a",
"parentId": "739",
"isLeaf": false,
"molecule": {
"id": "sa_9ae70c5f8c8f02f7fc61047a",
"inchikey": "NFVXWXBDIXHDLF-UHFFFAOYSA-N",
"smiles": "COCCOCOCCOc1ccc(N)cc1"
},
"smiles": "COCCOCOCCOc1ccc(N)cc1",
"reactionStepId": "sa_ea3b980f8ffe415c51e5bc1f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150374690A1;0442;1807079\",\"rsmi\":\"O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([O:10][CH2:9][CH2:8][O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:17][cH:16]1>CO.N#N.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH2:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([O:10][CH2:9][CH2:8][O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:17][cH:16]1>CO.N#N.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([NH2:15])[cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_ea3b980f8ffe415c51e5bc1f",
"reactionHash": "2277e062d357a3df3f313817877678ba129f644b0c0ef7629732412f1a32675a"
},
"children": [
{
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"routeId": "sa_58235ab7dcf90f2aaf4aed0f",
"moleculeId": "sa_e17384b5ed259a8dfd8e24fc",
"parentId": "740",
"isLeaf": false,
"molecule": {
"id": "sa_e17384b5ed259a8dfd8e24fc",
"inchikey": "UQXJFPWPXDMNKS-UHFFFAOYSA-N",
"smiles": "COCCOCOCCOc1ccc([N+](=O)[O-])cc1"
},
"smiles": "COCCOCOCCOc1ccc([N+](=O)[O-])cc1",
"reactionStepId": "sa_d464241e2931e832246e68b7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150374690A1;0441;1807078\",\"rsmi\":\"Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>CCCCCC.CCN(C(C)C)C(C)C.CCOC(C)=O.ClCCl.N#N.O.O=C(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1].[OH:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1>CCCCCC.CCN(C(C)C)C(C)C.CCOC(C)=O.ClCCl.N#N.O.O=C(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19]1\"}",
"reactionStep": {
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"reactionHash": "ed24b64d06ea5240c01591a14c28f424d6c85025e9c1ca4077426bcb29ed4b0f"
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"children": [
{
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"routeId": "sa_58235ab7dcf90f2aaf4aed0f",
"moleculeId": "sa_e1282bacce16e1c0d121bc00",
"parentId": "741",
"isLeaf": true,
"molecule": {
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"inchikey": "BIAAQBNMRITRDV-UHFFFAOYSA-N",
"smiles": "COCCOCCl"
},
"smiles": "COCCOCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "743",
"routeId": "sa_58235ab7dcf90f2aaf4aed0f",
"moleculeId": "sa_ed566d03b35dd3473c3a9020",
"parentId": "741",
"isLeaf": false,
"molecule": {
"id": "sa_ed566d03b35dd3473c3a9020",
"inchikey": "YAPAEYFBLRVUMH-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(OCCO)cc1"
},
"smiles": "O=[N+]([O-])c1ccc(OCCO)cc1",
"reactionStepId": "sa_5704de0c05d30f742ddbc8db",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150374690A1;0378;1807035\",\"rsmi\":\"F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:13][cH:12]1.[OH:8][CH2:9][CH2:10][OH:11]>CCCCCC.CCOC(C)=O.O.O=C(O)O.[Cs+].[Cs+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][OH:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"F[c:7]1[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:13][cH:12]1.[OH:8][CH2:9][CH2:10][OH:11]>CCCCCC.CCOC(C)=O.O.O=C(O)O.[Cs+].[Cs+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][OH:11])[cH:12][cH:13]1\"}",
"reactionStep": {
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"moleculeId": "sa_daa2686ce35f5333036b911a",
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"isLeaf": true,
"molecule": {
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"inchikey": "LYCAIKOWRPUZTN-UHFFFAOYSA-N",
"smiles": "OCCO"
},
"smiles": "OCCO",
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"template": null,
"metadata": null,
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},
{
"id": "745",
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"moleculeId": "sa_2e6e1876b01a035271190a1c",
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"molecule": {
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"inchikey": "WFQDTOYDVUWQMS-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(F)cc1"
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"smiles": "O=[N+]([O-])c1ccc(F)cc1",
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},
{
"id": "746",
"routeId": "sa_58235ab7dcf90f2aaf4aed0f",
"moleculeId": "sa_c7f1a0b97d0719e5340edae9",
"parentId": "739",
"isLeaf": false,
"molecule": {
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"inchikey": "ULDJKHWMHJTUFQ-UHFFFAOYSA-N",
"smiles": "CN(C(=O)OC(C)(C)C)c1cccc(Nc2nc(Cl)ncc2F)c1"
},
"smiles": "CN(C(=O)OC(C)(C)C)c1cccc(Nc2nc(Cl)ncc2F)c1",
"reactionStepId": "sa_75c580be8ba54f5fe785571b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150374690A1;0446;1807082\",\"rsmi\":\"Cl[c:14]1[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]1[F:21].[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:10]1[cH:11][c:12]([NH2:13])[cH:22][cH:23][cH:24]1>CCCCCC.CCCCO.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:10]1[cH:11][c:12]([NH:13][c:14]2[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]2[F:21])[cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Cl[c:14]1[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]1[F:21].[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:10]1[cH:11][c:12]([NH2:13])[cH:22][cH:23][cH:24]1>CCCCCC.CCCCO.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:10]1[cH:11][c:12]([NH:13][c:14]2[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]2[F:21])[cH:22][cH:23][cH:24]1\"}",
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"molecule": {
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"inchikey": "QCTXBRCQBZFXDX-UHFFFAOYSA-N",
"smiles": "CN(C(=O)OC(C)(C)C)c1cccc(N)c1"
},
"smiles": "CN(C(=O)OC(C)(C)C)c1cccc(N)c1",
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{
"id": "748",
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"molecule": {
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"inchikey": "WHPFEQUEHBULBW-UHFFFAOYSA-N",
"smiles": "Fc1cnc(Cl)nc1Cl"
},
"smiles": "Fc1cnc(Cl)nc1Cl",
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]
}
}